Lithium Hydroxide → 3-{3-[3-t-Butyl-5-(4-chloro-benzoylamino)-pyrazol-1-yl]-phenyl}-propionic acid

HRID 1392315

Reaktionsgleichung

Reaktionsgleichung von HRID 1392315
C([O:3][C:4](=[O:32])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[C:17]([NH:18][C:19](=[O:27])[C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[CH:16][C:15]([C:28]([CH3:31])([CH3:30])[CH3:29])=[N:14]2)[CH:8]=1)C.[Li+].[OH-]>CO>[C:28]([C:15]1[CH:16]=[C:17]([NH:18][C:19](=[O:27])[C:20]2[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=2)[N:13]([C:9]2[CH:8]=[C:7]([CH2:6][CH2:5][C:4]([OH:32])=[O:3])[CH:12]=[CH:11][CH:10]=2)[N:14]=1)([CH3:31])([CH3:29])[CH3:30]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 588428933-{3-[3-t-Butyl-5-(4-chloro-benzoylamino)-pyrazol-1-yl]-phenyl}-propionic acid ethyl ester

Produkt 1

HCID 184498903-{3-[3-t-Butyl-5-(4-chloro-benzoylamino)-pyrazol-1-yl]-phenyl}-propionic acidAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of Example 158 (45 mg, 0.1 mmol) arid 2N LiOH (3 mL) in MeOH (3 mL) was stirred at RT overnight. The reaction mixture was neutralized to pH=4, and extracted with ethyl acetate (3×20 mL). The combined organic extracts were washed with brine, and dried (NaSO4) and filtered. The filtrate was concentrated to afford 3-{3-[3-t-butyl-5-(4-chloro-benzoylamino)-pyrazol-1-yl]-phenyl}-propionic acid, (38.5 mg, 87%). 1H NMR (DMSO-d6): 10.38 (s, 1H), 7.85 (d, J=8.4 Hz, 1H), 7.56 (d, J=8.4 Hz, 2H), 7.39 (s, 1H), 7.32 (d, J=4.8 Hz, 2H), 7.15 (t, J=4.8 Hz, 1H), 6.38 (s, 1H), 2.80 (t, J=7.6 Hz, 2H), 2.44 (t, J=7.2 Hz, 2H), 1.29 (s, 9H); MS (ESI) m/z: 426 (M+H+).

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (NaSO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-22cc03c3f7934a13a55c168c53b8ef99
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342037B2

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